Acetic Anhydride → HCID 67357344、化合物

HRID 889439ノート

反応式

HRID 889439 の反応式
[NH2:1][C:2]1[CH:7]=[C:6]([N+:8]([O-:10])=[O:9])[CH:5]=[CH:4][C:3]=1[C:11]([N:13]1[CH2:18][CH2:17][N:16]([CH3:19])[CH2:15][CH2:14]1)=[O:12].[C:20]([O:23][C:24](=O)C)(=[O:22])C>C(Cl)Cl.CN(C1C=CN=CC=1)C>[CH3:19][N:16]1[CH2:17][CH2:18][N:13]([C:11]([C:3]2[CH:4]=[CH:5][C:6]([N+:8]([O-:10])=[O:9])=[CH:7][C:2]=2[NH:1][C:20](=[O:22])[O:23][CH3:24])=[O:12])[CH2:14][CH2:15]1

参加物

5

反応物 2

HCID 7918Acetic AnhydrideHCID 59313927HCID 59313927、化合物

生成物 1

HCID 67357344HCID 67357344、化合物収率 96%

試薬・触媒・溶媒 2

HCID 142844-(Dimethylamino)pyridine触媒HCID 6344Dichloromethane溶媒

実験手順

To a solution of Intermediate 69B (540 mg, 2.04 mmol) in DCM (20 mL) was added TEA (0.570 mL, 4.09 mmol), acetic anhydride (0.289 mL, 3.06 mmol), and DMAP (2 mg, 0.016 mmol). The reaction mixture was stirred overnight, then washed with saturated aqueous NaHCO3, dried, and concentrated. The reaction mixture was purified by flash chromatography, (SiO2, 24 g, 0-10% MeOH/DCM) to give Intermediate 69C (600 mg, 96%) as a yellow solid. HPLC: Rt=0.517 min. (CHROMOLITH® column 4.6×50 mm eluting with 10-90% aqueous methanol over 4 min. containing 0.1% TFA, 4 mL/min., monitoring at 220 nm). MS (ES): m/z=307 [M+H]+.

後処理

  1. washwashed with saturated aqueous NaHCO3
  2. customdried
  3. concentrationconcentrated
  4. customThe reaction mixture was purified by flash chromatography, (SiO2, 24 g, 0-10% MeOH/DCM)

出典と根拠

ORDレコード
ord-27d98686fd7a4195970f8c6005f18ae5
出典データセット
uspto-grants-2012_08
特許番号
US08252795B2

反応ノート

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